Towards Storage of Solar Energy in Photochromic Molecules: Benzannulation of the Dihydroazulene/Vinylheptafulvene Couple

Anders Bo Skov; Johannes Fabritius Petersen; Jonas Elm; Benjamin N. Frandsen; Marco Santella; Martin Drøhse Kilde; Henrik Grum Kjærgaard; Kurt Valentin Mikkelsen; Mogens Brøndsted Nielsen

doi:10.1002/cptc.201600046

Towards Storage of Solar Energy in Photochromic Molecules: Benzannulation of the Dihydroazulene/Vinylheptafulvene Couple

Anders Bo Skov, Johannes Fabritius Petersen, Jonas Elm, Benjamin N. Frandsen, Marco Santella, Martin Drøhse Kilde, Henrik Grum Kjærgaard, Kurt Valentin Mikkelsen, Mogens Brøndsted Nielsen

Department of Chemistry

15 Citations (Scopus)

Abstract

One challenge in the development of molecular photoswitches for solar energy storage is to increase the energy of the isomer formed upon irradiation. This work focuses on how to affect the relative stabilities of the isomers of the dihydroazulene/ vinylheptafulvene (DHA/VHF) couple by combining the light-induced DHA to VHF conversion with the loss of aromaticity. We present a synthetic procedure for benzannulation of DHA at the C7−C8 bond, with the key steps being a stereoselective Diels–Alder cycloaddition followed by an oxidation. The optical properties and switching abilities of this compound are described in a combined theoretical and experimental study. Calculations support that benzannulation serves to increase the overall energy capacity of the photoswitch by stabilizing the DHA and destabilizing the VHF.

Original language	English
Journal	ChemPhotoChem
Volume	1
Issue number	5
Pages (from-to)	206-212
Number of pages	7
ISSN	2367-0932
DOIs	https://doi.org/10.1002/cptc.201600046
Publication status	Published - 1 May 2017

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title = "Towards Storage of Solar Energy in Photochromic Molecules: Benzannulation of the Dihydroazulene/Vinylheptafulvene Couple",

abstract = "One challenge in the development of molecular photoswitches for solar energy storage is to increase the energy of the isomer formed upon irradiation. This work focuses on how to affect the relative stabilities of the isomers of the dihydroazulene/ vinylheptafulvene (DHA/VHF) couple by combining the light-induced DHA to VHF conversion with the loss of aromaticity. We present a synthetic procedure for benzannulation of DHA at the C7−C8 bond, with the key steps being a stereoselective Diels–Alder cycloaddition followed by an oxidation. The optical properties and switching abilities of this compound are described in a combined theoretical and experimental study. Calculations support that benzannulation serves to increase the overall energy capacity of the photoswitch by stabilizing the DHA and destabilizing the VHF.",

author = "Skov, {Anders Bo} and Petersen, {Johannes Fabritius} and Jonas Elm and Frandsen, {Benjamin N.} and Marco Santella and Kilde, {Martin Dr{\o}hse} and Kj{\ae}rgaard, {Henrik Grum} and Mikkelsen, {Kurt Valentin} and Nielsen, {Mogens Br{\o}ndsted}",

year = "2017",

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doi = "10.1002/cptc.201600046",

language = "English",

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journal = "ChemPhotoChem",

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T2 - Benzannulation of the Dihydroazulene/Vinylheptafulvene Couple

AU - Skov, Anders Bo

AU - Petersen, Johannes Fabritius

AU - Elm, Jonas

AU - Frandsen, Benjamin N.

AU - Santella, Marco

AU - Kilde, Martin Drøhse

AU - Kjærgaard, Henrik Grum

AU - Mikkelsen, Kurt Valentin

AU - Nielsen, Mogens Brøndsted

PY - 2017/5/1

Y1 - 2017/5/1

N2 - One challenge in the development of molecular photoswitches for solar energy storage is to increase the energy of the isomer formed upon irradiation. This work focuses on how to affect the relative stabilities of the isomers of the dihydroazulene/ vinylheptafulvene (DHA/VHF) couple by combining the light-induced DHA to VHF conversion with the loss of aromaticity. We present a synthetic procedure for benzannulation of DHA at the C7−C8 bond, with the key steps being a stereoselective Diels–Alder cycloaddition followed by an oxidation. The optical properties and switching abilities of this compound are described in a combined theoretical and experimental study. Calculations support that benzannulation serves to increase the overall energy capacity of the photoswitch by stabilizing the DHA and destabilizing the VHF.

AB - One challenge in the development of molecular photoswitches for solar energy storage is to increase the energy of the isomer formed upon irradiation. This work focuses on how to affect the relative stabilities of the isomers of the dihydroazulene/ vinylheptafulvene (DHA/VHF) couple by combining the light-induced DHA to VHF conversion with the loss of aromaticity. We present a synthetic procedure for benzannulation of DHA at the C7−C8 bond, with the key steps being a stereoselective Diels–Alder cycloaddition followed by an oxidation. The optical properties and switching abilities of this compound are described in a combined theoretical and experimental study. Calculations support that benzannulation serves to increase the overall energy capacity of the photoswitch by stabilizing the DHA and destabilizing the VHF.

U2 - 10.1002/cptc.201600046

DO - 10.1002/cptc.201600046

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JF - ChemPhotoChem

IS - 5

ER -

Towards Storage of Solar Energy in Photochromic Molecules: Benzannulation of the Dihydroazulene/Vinylheptafulvene Couple

Abstract

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